Organic insecticide



Patented Apr. 25, 1944 2,341,317 onesmc msnc'rromn James William Swaine, Bayside, N. Y., assignor to General Chemical Company, New York, N. Y.,' a corporation or New York No Drawing. Application May 4, 1938,

Serial No. 205,991

8 Claims.

This invention relates in insecticides for controlling codling moth larvae.

In accordance with the present invention it has been found that compounds containing the .xanthone structure possess toxicit against codmore of the hydrogens in the compounds of (a) and (b).

The insecticides of the presen invention may be applied to fruit, foliage, or at er food of codling moth larvae. They are compatible with and therefore may be used in combination with other stomach insecticides, contact insecticides, fungicides, and the supplementarymaterials such as hydrated lime, diluents, sticking, spreading, and wetting agents, etc., except oils, commonly used in combination with stomach poison insecticides. They may be used dispersed in liquids or in dry form asdusts.

The compounds of the present invention have been'found to be relatively stable under the usual conditions of use as compared with previously proposed organic insecticides and for this reason better retain their high toxicity to codling moth larvae. Furthermore, the compounds of the present invention, especially those containing in the molecule only carbon, hydrogen, and oxygen, are, as a class, relatively non-toxic to warmblooded animals and human beings; hence they.

may be applied to edible plants without danger of poisoning, such as attends the use of lead arsenate and other formerly known insecticides.

The preferred compounds of the present invention are those of low volatility and very low solubility in water. These properties permit the retention of the insecticides on foliage or fruit, etc., to which they are applied, for relatively long periods and hence the period between applications may be extended and the dosage lowered as compared with compounds which readily evaporate from treated plants or are easily washed therefrom by rain.

It has been found that for combatting codling moth larvae xanthone is outstandingly superior even to most of the other insecticides of the invention. In the past leader-senate has been the most eilective insecticide available against this pest. However, the application oi lead arsenate to the host, for instance to pome fruit trees. has always been objectionable in view of the hishly poisonous nature of compound and the possibility that traces may remain upon edible portions of the plant to which it is applied. Accor ly the use of lead arsenate as a late season sp ay has been particularly dangerous from this standpoint.

Xanthone, on the other hand, has been found not onlyto be at least the equal of lead arsenate as a codling moth larvicide, but to be entirely free from any danger to human beings if taken internally even in amounts greatly in excess of those which may normally remain on edible portions of sprayed plants and fruits. Xanthone, furthermore, has been found to be substantially innocuous to plants. to which it has been applied;

, in conducting comparative tests of xanthone with lead arsenate upon pome fruit trees it was observed that the plants to which the xanthone had been applied were in a healthier, more vigorous and flourishing condition than those upon which lead arsenate had been used.

The following table demonstrates the efiectlve ness of the insecticides of the present invention.

The toxicity of the individual insecticides is ex-' pressed in the table in terms of per cent of larvae dead at the end of ten days. Check tests without insecticide were run for comparative purposes.

From the above table it'will be apparent that the presence of substituent froups in xanthone, while it may reduce the toxicity, does not destroy it entirely and the substituted xanthones, particularly the xanthione and the 3-bromo-xanthone,

retain in a large measure the toxicity of the parent compound.

The iollowing results were obtained in field tests in the State of Washington comparing nanthone, and lead arsenate for codling moth control in seven diflerent treatments or wineaap apple trees. Both insecticides were applied to the trees as suspensions in water-lead arsenate in combination with one pint or mineral oil, 1 pint or kerosene, and pound oi a spreading agent per 100 gallons of water: xanthone in combination with pound of hydrated lime and one pound of tar soap per 100 gallons of water. A lead arsenate calyx spray, which was uniform for all treatments, was applied about the middle of May and seven cover sprays were applied distributed through the period from about May 24 to about the middle of August.

' is expressed in terms of larvae killed.

- Table No. 3

per cent of codling moth Lead mounts Concenmm Xanthone OOH 5 7 7 eck xanthone structure and such commonly used sup- Table No. 2

Lead arsenate Xanthone -T m Per cent Mean Mm 233% Per cent Yer cent Per cent Per cent U. S. Number dosage Number dosage apples smug injured clean ga; o! sprays per 100 of sprays per 100 gallons gallons 7 Pounds Pound: 8 3 11, 906 20. 8 5. 5 24. 3 75. 7 98. 2 6 3 2 3 11, 389 -10. 2 5. 2 l4. 4 85. 6 94. 4 3 3 5 8 14, 267 2. 6 3. 6 5. 7 94. 3 96. 3 3 3 5 2.1 13,888 1.9 3.7 5.1 94.9 $6.3 l 3 7 3 16, 058 0. 5 1. 6 2. 0 98. 0 98. 4 l 3 7 Z 36 v 10, 992 0. 6 4. 2 4. 6 95. 4 Q5. 8 l 3 7 3 11, 862 0. 3 1.8 2. l 97. 9 98. 2

It will be noted from the above table that in piementary materials as may be desired to imeach of the last three tests reported, an initial lead arsenate calyx spray was followed by seven xanthone cover sprays; in the third and fourth tests, numbering the tests consecutively from top to bottom of the table, the first three sprays applied to the trees were lead arsenate sprays, followed by five sprays of xanthone, and in the second test reported the first six sprays were lead arsenate and the last two sprays were xanthone sprays. The method of controlling codling moth larvae involving the spraying of the trees during the growth of the calyx with lead arsenate and thereafter, during the growth of the fruit, spraying the trees with a compound containing the xanthone structure such as xanthone, is an important feature of this invention.

Conventional measures of efliciency are used in the above table to allow comparison of the diiferent treatments. A stung apple is one bearing one or more of the shallow injuries made by a codling moth larva killed while eating into the apple. A wormy" apple is one bearing one or more of the deep injuries made by a codling moth larva which successfully eats into the core of the apple. An injured apple is one bearing one or more codling moth injuries of either type. A clean apple bears no codling moth injury of any type. A U. S. No. 1 grade apple, with respect to codling moth injury, may be either a clean apple or one bearing no more than two sting injuries and no worm" injuries. Apples bearing worm injuries or more than two sting injuries go into lower grades than U. S. No. 1.

' Xanthone tested against lead arsenate in the laboratory, employing various dilutions, showed marked superiority to the lead arsenate in retaining it toxicity as concentration diminished. The following table demonstrates this characteristic. The compounds were tested in the manner set forth in connection with Table No. 1 above using aqueous suspensions of the insecticide. Toxicity prove control. For example, xanthone has been used successfully in combination with sulfur and copper fungicides to give simultaneous control of codling moth and apple diseases, and in combination with hydrated limeand tar soap to give a heavy, smooth deposit resistant to removal by rain.

I claim: 1

1. The method of combatting codling moth larvae infestations on pome fruit trees, which comprises spraying the trees during the growth of the calyx with lead arsenate, and thereafter during the growth of the fruit spraying the trees larvae infestations on pome fruit trees, which comprises applying lead arsenate to the trees during the growth of the calyx, and thereafter during the growth of the fruit'applying to the trees a compound having the xanthone structure as the essential insecticidal material for combatting codling moth larvae infestations, the amount of lead arsenate and compound having the xanthone structure thus applied to the trees being controlled so as to eilectively-protect the bulk of the fruit on the trees throughout its growth against attack by codling moth larvae and to leave an amount of lead arsenate on the fruit when picked such as to be substantially non-injurious to human beings.

4. The method as defined in claim 1 in which the compound containing the xanthone structure is a halogenated xanthone.

6. The method as defined in claim 1 in which the compound containing the xanthone structure is an alkyl xanthone.

7. The method of combatting codling moth 8. A method of combatting codlinz moth larvae infestations on pome fruit trees, which comprises applying lead arsenate to the trees during the growth of the calyx, and thereafter during the larvae infestations on pome fruit trees which 5 growth of the fruit applying xanthone to the comprises spraying the trees during the growth of the calyx with lead arsenate, and thereafter,

v during the growth of the fruit. spraying the trees with a compound of the group consisting of xanthones and xanthiones. 10

trees.

JAMES WILLIAM SWAINE. 

